I had the thankless task of being executor for my parents' estate. I distinctly remember the Florida HOA that made that so much worse.

After expressing their utmost sympathies and saying they'd help any way they could, mere weeks later they put a legal "estoppel" on the sale of the house due to some overgrown vines(?), which of course, were never mentioned by anyone.

This is not possible and maybe mixing terms. HOA has to disclose an existing violation as part of the estoppel process. Estoppel is just a disclosure certificate not a legal hold